Kingston, the hemisphere’s largest English-speaking city south of Miami, is a study in contrasts. Gaudy mansions sit next to ramshackle “cardboard villas,” and fine arts museums jostle for space with garish dance halls and clubs. For business travelers and tourists, Kingston takes all this and blends it together into a uniquely funky salad.
1. Drop in on the King of Reggae. Visit the late Bob Marley’s home and studio at 56 Hope Road, 10 to 15 minutes by cab from New Kingston’s hotel district. Bullet holes in the rear wall from a 1976 assassination attempt are a reminder of the tumultuous era in which he made his name.
2. Join the Paartaay! On summer weekends, enterprising young promoters put on fêtes-for-pay, many with themes echoing Ibiza or Amsterdam—topped by drink-inclusive cover charges and heavily discounted ladies’ nights. Admission ranges from $16 to $35, but the bar never closes.
3. Mix Pirates and Seafood. Infamous pirate haven Port Royal on Kingston Harbor Shore Road is also a spot to sample some of the sea’s most delectable riches. If you’re in Kingston for the city’s annual Seafood Festival (second week of October), Gloria’s restaurant is the best place to put down your anchor.
4. See the City—from Above. At Strawberry Hill, 4,000 feet atop a winding Blue Mountain road, music and hotel magnate Chris Blackwell’s Island Outpost chain gives visitors a majestic panorama of Kingston and the shimmering Caribbean Sea. The restaurant and accommodations are pricey, but the budget-conscious can skip those and just get a quick cup of joe on the way up at Café Blue.
5. See the Sport of Kings. Jamaica’s premier horse-racing track, Caymanas Park, is only a 20-minute taxi ride from downtown Kingston, taking you past swampland and sugarcane fields. A three-race series takes place in mid-June with the Jamaica Derby. Admission on race days runs about $1.50.
6. Watch Cricket. Jamaicans’ favorite sport attracts test match cricket fans from across the Caribbean during the summer months at Sabina Park, when the combined West Indies team plays visitors from Pakistan, India and Australia. An equal attraction: the special party section known as “the Mound,” where the liquor flows nonstop when play halts between bowling spells (six balls, pitched overarm, are an “over” or bowling spell). Taxis to the stadium cost $4.
7. Parade Downtown. Just a couple blocks west of the bus terminal square called “the Parade” lies the colorful Coronation street market. When the shopping’s done, double back to the Parade to tour the rest of the city in the new bright yellow municipal buses. Best of all: bus fares cost $1.50.
8. Catch Some Live Music. If your appetite for Jamaica’s foremost music export has been whetted by the visit to Marley’s studio, visit the live clubs where reggae is making a modern-day comeback. Best choice: The Quad, a multi-level nightclub in the middle of New Kingston’s nightlife strip. Cover charge: $5.
9. Check Out the Museums. Many visitors overlook Kingston’s cultural and historical repositories, such as The National Gallery, the Bank of Jamaica’s Money Museum and The Institute of Jamaica—all within easy walking distance of Kingston’s downtown district. Open weekdays (The National Gallery is closed on Mondays) from 10 a.m. to 4 p.m. Entry fees range from $2 to $4.
10. Eat the “World’s Fastest Meal.” Usain Bolt, the world’s fastest man, has opened Jamaica’s newest themed eatery, called Tracks & Records, at the northwest end of the city’s midtown shopping district. The restaurant offers Olympic-sized sports viewing, coupled with the latest audio and Internet offerings, and classic bar food with a Jamaican twist—jerk chicken spring rolls.